Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary

Takamatsu, Kazutaka; Hayashi, Yoshihiro; Kawauchi, Susumu; Hirano, Koji; Miura, Masahiro

doi:https://doi.org/10.1021/acscatal.9b01145

Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary

Takamatsu, Kazutaka; Hayashi, Yoshihiro; Kawauchi, Susumu et al.

ACS Catalysis, 2019, 9(6), 5336-5344

Number of Access:178（2025-07-17 20:43 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92706

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Title	Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary
Creator	CreatorName Takamatsu, Kazutaka
	NRID 1000080739029 1000080739029 CreatorName Hayashi, Yoshihiro
	NRID 1000080204676 1000080204676 CreatorName Kawauchi, Susumu
	NRID 1000070532696 1000070532696 ORCID 0000-0001-9752-1985 0000-0001-9752-1985 researchmap permalink koj koj Scopus Author ID 7402407063 7402407063 CreatorName Hirano, Koji
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 CreatorName Miura, Masahiro
Subject	amination
	bidentate auxiliary
	C-H functionalization
	copper
	phenols
Description	Takamatsu K., Hayashi Y., Kawauchi S., et al. Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary. ACS Catalysis. 9(6), 5336-5344 (2019), 7 June 2019; © 2019 American Chemical Society. https://doi.org/10.1021/acscatal.9b01145.
Abstract	A copper-catalyzed regioselective direct amination of phenol derivatives with diarylamines via phenanthroline-based bidentate auxiliary-directed C-H cleavage has been developed. This reaction proceeds smoothly with only a copper salt and air as a terminal oxidant to produce the corresponding o-aminophenols in good yields. Moreover, the directing group can be easily attached, detached, and recycled. Additionally, preliminary computational studies of the reaction with DFT have also been performed.
Publisher	American Chemical Societyservice@acs.org
Source Title	ACS Catalysis
Volume (Issue)	9(6)
Page	5336-5344
Date of Issued	2019-01-07
Language	English
Handle URL	https://hdl.handle.net/11094/92706
eISSN	21555435
NCID	AA12599706
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acscatal.9b01145
Access Rights	open access
CopyRight	© 2019 American Chemical Society.
CopyRight	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, ACS Catalysis, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b01145.
oaire:version	Accepted Manuscript
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	ACS Catalysis. 2019, 9(6), p. 5336-5344
DC.title	Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary
DC.creator	Takamatsu, Kazutaka
	Hayashi, Yoshihiro
	Kawauchi, Susumu
	Hirano, Koji
	Miura, Masahiro
DC.publisher	American Chemical Societyservice@acs.org
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2019-01-07
DC.identifier	https://doi.org/10.1021/acscatal.9b01145
DC.subject	amination
	bidentate auxiliary
	C-H functionalization
	copper
	phenols
DC.description	Takamatsu K., Hayashi Y., Kawauchi S., et al. Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary. ACS Catalysis. 9(6), 5336-5344 (2019), 7 June 2019; © 2019 American Chemical Society. https://doi.org/10.1021/acscatal.9b01145.
DCTERMS.abstract	A copper-catalyzed regioselective direct amination of phenol derivatives with diarylamines via phenanthroline-based bidentate auxiliary-directed C-H cleavage has been developed. This reaction proceeds smoothly with only a copper salt and air as a terminal oxidant to produce the corresponding o-aminophenols in good yields. Moreover, the directing group can be easily attached, detached, and recycled. Additionally, preliminary computational studies of the reaction with DFT have also been performed.
DC.rights	© 2019 American Chemical Society.
DC.rights	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, ACS Catalysis, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b01145.
DC.format	92706
citation_title	Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary
citation_author	Takamatsu, Kazutaka
	Hayashi, Yoshihiro
	Kawauchi, Susumu
	Hirano, Koji
	Miura, Masahiro
citation_publisher	American Chemical Societyservice@acs.org
citation_language	English
citation_date	2019-01-07
citation_journal_title	ACS Catalysis
citation_volume	9
citation_issue	6
citation_firstpage	5336
citation_lastpage	5344
citation_doi	https://doi.org/10.1021/acscatal.9b01145
citation_public_url	https://hdl.handle.net/11094/92706

Copper-Catalyzed Regioselective C-H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary

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